mail-send

name	mail-send
model	haiku
description	Send emails with attachments via Apple Mail AppleScript automation. Prepares a visible draft for user review before sending. Use when sending emails with file attachments. Triggers on send email, mail send, email with attachment, mail schicken.
disableModelInvocation	true
requires_standards	["english-only"]

mail-send

Sends emails with attachments via Apple Mail (Mail.app) using AppleScript automation.

When to Use

• User wants to send an email with one or more file attachments
• User says "send email", "mail send", "email with attachment"
• User says "e-mail senden", "mail schicken", "email verschicken"
• Fastmail MCP send_email cannot be used because attachments are required

Do NOT

• Do NOT send emails without presenting the draft for user review first
• Do NOT use for emails without attachments — use Fastmail MCP tools instead

Accounts

The user's email accounts in Apple Mail:

Address	Purpose
[e-mail]	Business / geschäftlich
[e-mail]	Private / persönlich

Note: Gmail is a legacy account — never use it as sender.

IMPORTANT: Always set the sender property to select the correct From address. Without it, Apple Mail defaults to the last-used account (often Gmail).

Context	Use sender
Business / geschäftlich	[e-mail]
Private / persönlich	[e-mail]

Default (if unclear): [e-mail]

AppleScript Template

tell application "Mail"
    activate
    set newMessage to make new outgoing message with properties {subject:"SUBJECT", content:"BODY", visible:true, sender:"[e-mail]"}
    tell newMessage
        make new to recipient at end of to recipients with properties {address:"[e-mail]"}
        -- Optional CC:
        -- make new cc recipient at end of cc recipients with properties {address:"[e-mail]"}
        make new attachment with properties {file name:POSIX file "/absolute/path/to/file.pdf"}
        -- Additional attachments:
        -- make new attachment with properties {file name:POSIX file "/absolute/path/to/file2.pdf"}
    end tell
end tell

Usage Pattern

Run via osascript heredoc. See scripts/send-draft.sh for the single-recipient, single-attachment pattern.

Multiple Recipients and Multiple Attachments

See scripts/send-draft-multi.sh for the multi-recipient, multi-attachment pattern (to, cc, and multiple file attachments).

Long Bodies and Umlauts / Special Characters (MANDATORY PATTERN)

Problem: Apple Mail via AppleScript is extremely sensitive to:

1. Encoding: read POSIX file "..." defaults to MacRoman. UTF-8 bytes get interpreted as multi-byte glyphs, producing garbled output like ä for ä, — for —, or " for „. German text, em-dashes, curly quotes, and bullets (•) all break this way.
2. Inline heredoc quoting: Large bodies with German punctuation or nested quotes frequently trip the AppleScript parser with cryptic errors like syntax error: Unknown token found. Line-length and quote-escaping are both fragile.

Mandatory pattern for any body with umlauts, em-dashes, curly quotes, or > ~20 lines:

Step 1 — write the body to a UTF-8 file via the Write tool (never via echo > file in Bash, which may drop encoding):

Write → /tmp/mail-body.txt  (UTF-8, full email body)

Step 2 — run AppleScript that reads the file with the explicit UTF-8 class via a separate .applescript file (heredoc + AppleScript heredoc + UTF-8 marker don't coexist reliably). See scripts/send-draft-utf8.sh for the full pattern.

The as «class utf8» clause is non-optional — omitting it produces the MacRoman-interpretation garbage. The guillemets around class utf8 are part of the AppleScript syntax (option-backslash / option-shift-backslash on a German keyboard, or pasted literally).

Expected output: osascript returns the string missing value on success. This is not an error — AppleScript's make returns a message reference, which osascript prints as missing value when returned to the shell.

Rules

• Always use visible:true — creates a visible draft for user review, never auto-sends
• File paths must be absolute POSIX paths (e.g. /Users/malte/Documents/file.pdf)
• Never use relative paths in the file name property
• For bodies with German text, em-dashes, curly quotes, bullets, or > ~20 lines: always use the file + UTF-8 pattern above. Inline heredoc bodies are only safe for short ASCII-only content (subject confirmations, one-liners).

DO NOT

• Do NOT use Spark for AppleScript automation — Spark has no AppleScript dictionary
• Do NOT auto-send emails — always create a visible draft for user review
• Do NOT use Fastmail MCP send_email for emails with attachments (no attachment support)
• Do NOT use relative file paths in the attachment file name property
• Do NOT inline long bodies with umlauts in a Bash heredoc — AppleScript will mangle the encoding. Use the file + read as «class utf8» pattern.
• Do NOT use read POSIX file "..." without the as «class utf8» clause when the body contains non-ASCII characters.